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Ligand structures of synthetic deoxa-pyranosylamines with raucaffricine and strictosidine glucosidases provide structural insights into their binding and inhibitory behaviours.

Xia, Liqun and Lin, Haili and Staniek, Agata and Panjikar, Santosh and Ruppert, Martin and Hilgers, Petra and Williardt, Jörg and Rajendran, Chitra and Wang, Meitian and Warzecha, Heribert and Jäger, Volker and Stöckigt, Joachim (2015):
Ligand structures of synthetic deoxa-pyranosylamines with raucaffricine and strictosidine glucosidases provide structural insights into their binding and inhibitory behaviours.
In: Journal of enzyme inhibition and medicinal chemistry, 30 (3), pp. 472-478. ISSN 1475-6374,
[Article]

Abstract

Abstract Insight into the structure and inhibition mechanism of O-β-d-glucosidases by deoxa-pyranosylamine type inhibitors is provided by X-ray analysis of complexes between raucaffricine and strictosidine glucosidases and N-(cyclohexylmethyl)-, N-(cyclohexyl)- and N-(bromobenzyl)-β-d-gluco-1,5-deoxa-pyranosylamine. All inhibitors anchored exclusively in the catalytic active site by competition with appropriate enzyme substrates. Thus facilitated prospective elucidation of the binding networks with residues located at <3.9 Å distance will enable the development of potent inhibitors suitable for the production of valuable alkaloid glucosides, raucaffricine and strictosidine, by means of synthesis in Rauvolfia serpentina cell suspension cultures.

Item Type: Article
Erschienen: 2015
Creators: Xia, Liqun and Lin, Haili and Staniek, Agata and Panjikar, Santosh and Ruppert, Martin and Hilgers, Petra and Williardt, Jörg and Rajendran, Chitra and Wang, Meitian and Warzecha, Heribert and Jäger, Volker and Stöckigt, Joachim
Title: Ligand structures of synthetic deoxa-pyranosylamines with raucaffricine and strictosidine glucosidases provide structural insights into their binding and inhibitory behaviours.
Language: English
Abstract:

Abstract Insight into the structure and inhibition mechanism of O-β-d-glucosidases by deoxa-pyranosylamine type inhibitors is provided by X-ray analysis of complexes between raucaffricine and strictosidine glucosidases and N-(cyclohexylmethyl)-, N-(cyclohexyl)- and N-(bromobenzyl)-β-d-gluco-1,5-deoxa-pyranosylamine. All inhibitors anchored exclusively in the catalytic active site by competition with appropriate enzyme substrates. Thus facilitated prospective elucidation of the binding networks with residues located at <3.9 Å distance will enable the development of potent inhibitors suitable for the production of valuable alkaloid glucosides, raucaffricine and strictosidine, by means of synthesis in Rauvolfia serpentina cell suspension cultures.

Journal or Publication Title: Journal of enzyme inhibition and medicinal chemistry
Journal volume: 30
Number: 3
Divisions: 10 Department of Biology
10 Department of Biology > Plant Biotechnology and Metabolic Engineering
Date Deposited: 07 Jul 2015 08:20
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